Ice colors of the acridone series



United States Patent ICE COLORS OF 'IfiE ACRIDONE SERIES Frederick Brody, New York, N. Y., assignor to American Cryalaamid Company, New York, N. Y., a corporation 0 aine No Drawing. Original application March 1, 1952, Serial No. 274,487, now Patent .No. 2,694,713, dated November 16, 1954. Divided and this application January I 12, 1954, Serial No. 403,661

3 Claims. (Cl. 260-152) This invention relates to azo coloring matters of the formula Nn I in which R is a lower alkyl group, are diazotizeu and coupled with ice color coupling components, a new series of azo coloring matters is produced. When the coupling components are arylides of 2-hydroxy-3-naphthoic acid, the coloring matters have an unusual greenish shade of blue with good fastness properties. These are the preferred embodiments of the invention which, however, is not limited to coloring matters obtained by coupling with these particular coupling components. In other words, the invention is not limited to the production of blue azo coloring matters, though these are of particular importance, because other shades are obtainable with other ice-color coupling components.

The amines which are diazotized to produce the diazo components entering into the coloring matters of the present invention are themselves new compounds. They are, however, not claimed in this application, forming the subject matter of my copending application, Serial No. 274,487, filed March 1, 1951, now Patent No. 2,694,713, of which the present application is a division.

The alkoxy groups in the coloring matters of the present invention may be methoxy, ethoxy, propoxy, etc., or other lower alkoxy groups, but the best and most useful coloring matters are. obtained from the methoxy compound, which therefore constitutes the preferred embodiment. The invention, however, is not limited to coloring matters containing the methoxy group.

it is an advantage of the present invention that the amino acridones can be diazotized by ordinary methods and require no special procedures. Also, these diazo compounds may be used in the various common ways for preparing azoic coloring matters. Thus, for example, they may be coupled with coupling components, particularly ice color components, to form dyestuffs or pig- 2,725,375 Patented Nov. 29, 1955 ice ments, or the coupling component can be padded on cloth and the coloring matter developed in the fiber. It is also possible to transform the diazo compounds into the diazoamino and other stable derivatives, so that they may be incorporated into a printing paste, the color being developed on the goods by acid development in the usual manner. v 7

Among the ice color coupling components which are particularly suitable for use'in coupling with the diazotized'compounds of the present invention are the following: beta-naphthol, 8-amino-2-naphthol, '8-acetylarnino- Z-naphthol, benzyl naphthols, pyrazolones and pyrazyl pyrazoloncs, hydroxybenzofluorenones; and the various N-substituted amides such as arylides of Z-hydroxy-3- naphthoic acid, of 2-hydroxy-3-anthroic acid, of methyl and dim-ethyl-salicylic acids, of hydroxybenzacridone carboxylic acids, of hydroxydibenzofuran carboxylic acids, of hydroxybenzothiophene carboxylic acids, of acetoacetic acid, of benzoylace'tic acid and the like.

This invention is further illustrated by the following examples. Where not otherwise noted, parts are by weight.

' Example] COOH OCHa I NH -NHco'cn= A mixture of 6.3 parts of 2,5-dimethoxy-4-aminoacetanilide, 6.03 parts of 2-bromobenzoic acid, 6.2 parts of anhydrous potassium carbonate, 0.05 part of copper powder, 0.05 part of iodine and 40 parts of anyl alcohol is refluxed until condensation is complete. The solvent is removed by steam distillation and the residual, black product recrystallized from a mixture of dioxane and water.

Example 2 NHCOCH:

Example 3 Hydrolysis of the product of Example 2 is readily carried out by refluxing in a solution prepared from 5 parts of potassium hydroxide, 4 parts of water and 16 parts alcohol. The product is isolated by drowning and filtration and may be recrystallized from butanol.

Example4 OCH:

' OH ONHOBHS NH OCH;

The above blue dyestuff is obtained by diazotizing the product of Example 3 in the ordinary Way with nitrite and acid and developing in the diazo solution a length of cotton cloth padded with an alkaline solution of 2-hydroxy-3-naphthoic anilide.

Example 5 OCzHs NE: I

The procedure of Examples 1-3 are followed, substituting 2,5-diethoxy-4-aminoacetanilide for the 2,5-dimethoxy-4-aminoacetanilide in Example 1. The resulting diethoxy acridone compound is obtained in good yield and can be used in the same manner as the product of Example 3. For instance, it may be diazotized and coupled with 2-hydroxy-3= naphthoic" anilide to produce a blue dyestufi, differing only slightly in shade from the product of Example 4. C

4 I claim: '1. An azo coloring matter of the formula 00 [I \UNQFRI NH/ I OR I in which R is a lower alkyl group and R1 is the residue of an ice-color coupling component of the naphthalene series.

2. An azo coloring matter of the formula in which R is lower alkyl.

3. An azo coloring matter of the formula No references cited. 

1. AN AZO COLORING MATTER OF THE FORMULA 